


A Master for a Rich Playboy

by NotSoClean (MrWilliamJamesBooma)



Category: Arrow (TV 2012)
Genre: Alternate Universe, Alternate Universe - Slavery, Anal Sex, BDSM, Barebacking, Collars, M/M, Master/Slave, Oral Sex, Public Nudity, Scat, Slavery, Watersports
Language: English
Status: Completed
Published: 2019-05-29
Updated: 2019-05-29
Packaged: 2020-03-27 14:46:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Rape/Non-Con
Chapters: 1
Words: 3,472
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19015060
Author URL: https://archiveofourown.org/users/MrWilliamJamesBooma/pseuds/NotSoClean
Summary: In a world where everyone is either a slave or a master, Oliver finds himself losing his title of Master and becoming his best friend's slave.





	A Master for a Rich Playboy

**Author's Note:**

> Author's Note:  
> This story switches back and forth between past and present. The story begins in present, but whenever you see the dotted lines it means it's switching from present to past or past to present. Really its not as complicate as I probably just made it sound.  
> Also for any one who has read the Teen Wolf AU Slave Series I wrote, this takes place in the same alternate universe as that series, although this story isnt going to overlap and cross or anything along those lines.

Oliver opened his eyes as he awoke. It was morning and sunlight was trying hard to break through the closed heavy draperies, causing the room to be very dim. Oliver didn’t dare move a muscle, he knew it would be very bad for himself if he were to wake Master Tommy from his slumber. Master's arms were wrapped strongly around Oliver's bare chest, their bodies pressed tight up against one another under the cream-colored sheets, Master Tommy's hard morning wood halfway embedded up Oliver's asshole.

The position Oliver was stuck in wasn’t the most comfortable, his body twisted a few different ways, however sleeping in Master's bed was a far improvement to sleeping on the floor. This was sort of a treat for Oliver, and he owed it all to Master Malcom. If Master Malcom hadn’t have taken Roy for the night, than Oliver would be down on the floor with his fellow slave.

A sudden assault began on Oliver's asshole, a stream of hot urine blasted out of the cock within him and began flooding his insides. Oliver clenched his teeth, this wasn’t the first time Master had done this to him, nor would it be the last. He tried his hardest to ignore and accept the fact that his bowels were filling with his master's morning piss. He couldn’t help but feel like nothing more than a living anal-urinal for his master.

"Morning Ollie" came Master Tommy's voice from behind Oliver.

\---------------------------------- 

The Ceremony had been held towards the middle of the first semester of their sophomore year of high school. It was no secret what awaited teens on this special day, everyone knew it was the day of reckoning, the day when they would all learn their fates in this cruel world. There were only two choices, two fates, and they weren't their own to choose, they were assigned to them. The tests they had taken all throughout their freshman year would determine whether they were to spend the rest of their days as free men and masters, or slaves to those free men. 

Oliver knew that the test's were pretty much the equivalent of horseshit, and it was usually just a random descion by said test overseers. He also knew he had no worries when it came to his fate, just like Tommy had no worries of his fate. They were sons of two of the most powerful and richest men in the city, and it was extremely rare for pedigree such as themselves to be assigned a life of slavehood, they were born masters thanks to their parents.

They learned rather quickly that day that they were both right in their thinking, and proceeded to the line on the left to learn who had been assigned to be their first slave. A new slave was always awarded to every new master, always of the same gender, but since at this school (like most school's in the country) two thirds of the students were assigned slave status, the leftovers would be auctioned off to the highest bidder to make some extra capital for the government. 

\-----------------------------------------

Master Tommy finished buttoning up his white, designer dress shirt that he had tucked into his designer dress pants. Oliver watched from the bed, knowing that once Master Tommy left he would have to begin his daily chores of vacuuming, doing Master Tommy's laundry, and other odds and end things. And since Roy wasn't back from his night with Master Malcom yet, Oliver knew there was a good possibility he might end up doing his fellow slave's chores also. 

Master Tommy buttoned his cuffs with the special silver 'M' cuff links (which had been a gift from his father) and turned to Oliver. Oliver could see Master Tommy's cock was hard, bulging out against the black fabric.

"How 'bout a blow job for good luck" Master Tommy said, and while it may have sounded like a mere request, Oliver knew it was more like an order, for if he dared to say no to his former friend than he would be punished severely. Master Tommy could be the nicest of masters one second, and the meanest of masters the next second. 

Oliver got down on his knees before his primary master, as his master allowed his cock to stick out through the zipper hole. Oliver took the decent-sized cock into his mouth, going slowly down the shaft until the whole thing was in his mouth and his nose was pressed into Tommy's pubic hair. He'd been forced to service much larger cocks than his master's before. Master Tommy had a cock of average size for their ethnicity, with an erection length of not quite six inches. Master Tommy's dad on the other hand had a massive member between his legs, just as Oliver use to have himself when he was still a free man.

Master Tommy placed his silk, red tie on as Oliver performed his oral duties. Next came the black suit jacket, and by the time Master Tommy was fully dressed, his cock was on the verge of release; over the past two years Oliver had grown to know well when his former friend was close to climax. Moments later Oliver was swallowing down his Master's seed. It amazed him how indifferent he was to this now when at first giving a guy a blowjob was utter torture.

Master Tommy patted Oliver on the head as he zipped himself up. Oliver couldn’t help but wonder why his master was dressed up so fancy, Master Tommy owned and ran a nightclub called Vernant (which they had both co-owned before Oliver was enslaved) and he didn’t need to dress up fancy for that.

Master Tommy left, and Oliver inserted his bright-red silicone plug into his ass before beginning his chores like a good domesticated slave. 

\-------------------------------

Oliver's first slave was a fellow classmate named Andrew Smithson. It was no surprise to Oliver that the kid became a slave, the kid was a weakling, skin and bones, while he stuttered and stayed to himself, and also had been constantly picked on and ridiculed since they had been in kindergarten. Oliver couldn’t believe that he had been given the runt of the slaves though while Tommy had managed to score the Football team captain/quarterback. 

Tommy had decided to send his new slave off for a month at Slave School to be trained and disciplined in whatever fields Tommy chose for the guy. Oliver had the money to send his off too, but he wanted to break this faggot in himself, so he skipped the optional schooling.

Oliver was a cruel master right from the get-go. He believed like most people did, once someone was a slave they were no better than garbage. He used his new slave as a human toilet, as a way to get his rocks off whenever he wanted. For him his slave was more of a toy than anything, something to do humiliating things to for his own amusement. And it's not like this Andrew kid could do anything about it, he, just like every slave had a special collar on, a collar which injected liquid into his neck and worked in other ways to make it so that a slave could not disobey their master no mater how much they desired to.

Oliver kept Andrew around for a year before selling him to some research center, and buying himself two new slaves without proper training.

\---------------------------------

Oliver sat on the marble floor of the Mansion's basement gym and watched his shirtless, sweaty master use one of the weight benches. Master Tommy tried to work out at least once a day, determined that himself and his slaves were going to stay in top shape. Before coming here, Oliver had been lanky, good looking but still skinny, but now Master Tommy had built him up to become the muscle god he was today with massive pecks and abs. Roy was the opposite though, Tommy had the younger guy always doing exercises that gave him muscle while keeping his boyish figure. 

A grunt filled the air from Master Tommy as he pushed the barbell with the large weights up and brought it back down to his chest. Master Tommy had been working out for nearly an hour now, as soon as Tommy had returned home from whereever he had been he had grabbed Oliver and brought him down here. Oliver would far rather be here though than at the Starling City fitness club where Master Tommy also liked to go to work out. Oliver hated being taken out in public by his master, hated having people see him led around by a leash like a dog, while being as naked as one too. He especially hated being forced to do life acts in front of people who use to be his peers.

Master Tommy pushed the barbell up once more before placing it in its resting place and sitting up. Master Tommy's body was drenched in sweat, and Oliver knew what that meant for him. This private gym had a locker-style shower area attached that Master Tommy could use to wash off with, but Oliver knew that his master wasn’t going to use that when Oliver was there to do the job.

Master Tommy went over to the green sofa against the mirror cladded wall and flopped down. He snapped his fingers once, not needing to use words to tell Oliver what to do next. 

Oliver went over to his master and began his next duty as a slave. He stuck out his tongue and began licking up Master Tommy's smooth chest, tasting every bit of the salty sweat as he used his tongue to give his master a tongue bath. He slowly worked his way up, making his way to the right nipple where he took it into his mouth and began to suck on it. The moan from Master Tommy's lips told Oliver his master was enjoying it, but Oliver already knew that. Master Tommy loved it when Oliver sucked on his nipples, and Oliver loved doing it, it was one of the few things left that he could do that made him still feel like a man, sure it was different from sucking on a woman’s tit, but it was still similar enough.

Oliver eventually moved past the nipples to lick the rest of his master's body clean, every inch including in-between the ass cheeks. Master Tommy began rambling on about the old days when they were still equals, and then about how good Oliver had it as a slave. The sad truth was, Oliver did have it good here, Master Tommy treated him far better than Oliver had ever treated any of his own slaves.

"How 'bout after this we go grab your brother Roy and play outside for a bit" Master Tommy said as Oliver began licking down his right leg. Roy wasn’t Oliver's brother, although Master Tommy referred to them as brothers in slaveship like many masters do. Oliver hadn’t seen Roy all day, and while he did enjoy (to his shame) his lone time with his master, he knew what Roy was probably going through with Master Malcom and knew the younger guy would enjoy a reprieve. Master Malcom seemed to have a thing for Roy, although he had taken Oliver a few times up to his play room and the senior Meryln made his son seem like the Saint of all Saints.

\---------------------------------------------

By the fifth year of being a master Oliver had gone through at least twenty different slaves, just one of the perks that having boat-loads of money gave you. He had always had a cruel streak, built up rage that seemed to come from no where, and his slave's were the perfect ones to release all his nasty on so that he could be loving and carrying to whatever chick he was dating. He liked his slaves young, would go and buy them on their first day and break them in, and once every last ounce of resistance was gone he sell them for a new one. It just wasn’t any fun if they weren’t fighting against it in some way on the inside. 

Everything changed for him though just a single week before his twenty-six birthday. It had taken him by complete surprise when Starling City Slave-Enforcement Task force had come barreling into his family's manor one night. They immediately cuffed Oliver and his father, and they would have gotten Thea and Oliver's mother too if they hadn’t been on a mysterious trip to Canada. That was the first time in Oliver's life he had ever been truly scared, there on his knees beside his father, knowing his life was over but not why. 

\---------------------------------------------

Oliver ran after the stick as fast as he could, not on two legs, but on all fours like a pitiful dog. Roy ran beside him, eager to get to the stick first, but there was no way Oliver was going to allow that. He did not want to be the loser.  
Roy got a sudden extra burst of speed and reached the stick first, which had landed in front of one of the oak trees in Master Tommy's back yard. Being on the edge of the city, the Merlyn's property spread out for two miles into the woods.

Roy grabbed the ordinary stick in his mouth and began his four legged run back towards their master. But Oliver was not going to let his former slave win yet again, and used his head to ram into Roy on his side, sending Roy onto his back and the stick into the grass. Oliver wasted no time grabbing the stick in his mouth and continued his mission.

Oliver ran with speed, with Roy back on his hands and knees and just behind him. Oliver couldn’t believe how fast he had become in the last two years. When Master Tommy had first came up with the ideal to make them play fetch not long after they got here (Master Tommy had got the ideal from reading 'Better Master Living Weekly'), Oliver was as slow as could be. He kept falling over and tripping himself trying to keep up with Roy who caught on right off the bat. But then Roy had been a slave for quite some time before Oliver, and Roy had experience being degraded by walking around like a dog. Roy always won, for the first year and a half it was that way, but now Oliver had the hang of this, and it was any slaves game.

Oliver reached Master Tommy and lifted his head as his Master took the stick from his mouth. He had won another round. Six wins for him, four for Roy. Oliver couldn’t be more proud of himself, even though his naked body was filthy with sweet and dirt, some of his lesser used joints hurt and he was breathing hard from the intense work out.

Master Tommy patted Oliver on the head and declared the elder slave the winner. Oliver was so happy to have won, for winners got a reward, but so did the loser, but Oliver definitely didn’t want the reward that Roy was going to get.

Roy got his reward first, as he laid down in the grass and Tommy sat down on the younger slave's face, forcing Roy’s mouth and nose up into Tommy's but cheeks.

Oliver sat down and watched his fellow slave and his Master. His cock was full of blood knowing what was coming for himself, and when Master Tommy gave him the nod he knew he could begin. It only took a few strokes for the pressure to build and himself to go into an intense orgasm, spitting out two weeks worth of cum that had built up within. It felt so great to be able to cum.

Master Tommy and Roy remained in the same position and Oliver knew what was happening from experience. The losers reward was more or less a punishment, they got to eat every bit of shit that Master Tommy had stored in his bowels. Sometimes Master Tommy had barely anything, but days like today it appeared that Master Tommy had a lot of shit for Roy to eat. Just another reason Oliver was happy to have won.

\------------------------------------------

The police had put Oliver and his father's trial on the fast track, trying to get a conviction as soon as they could. It was rare for a defendant to get off though even if they were innocent. The Meryln's came to their defense, but it wasn’t enough. Oliver's father had forged documents and laundered millions of dollars using each of the families bank accounts, and now Oliver and his father were going to be enslaved.

It didn’t matter that Oliver was clueless to what his father had been doing. His mother and sister taking off hadn’t helped his case and the jury didn’t believe him. 

A few days after the trial, Tommy came to Oliver’s cell and let him know what was going on. The judge had ordered Oliver to spend the rest of his life at a Slave House (it was a place where Masters could go and rent slaves for periods of time for so much money), but Malcom had pulled some strings and got the Judge to release Oliver as a slave to Tommy. It turned out his slave at the time of capture was going to be Tommy’s slave too, he'd be no better than Roy now.

Unfortunately, Malcom couldn’t save Oliver’s dad, or at least that’s what Oliver was told. He wasn’t so certain that was true, there’s been times when he swore he saw a glimpse of his father at the manor, although why they wouldn’t want Oliver to know that his dad was there too would be a mystery to him.

\-----------------------------------------

Oliver sat on Master Tommy's bare lap as he waited for the film to start. Tonight was movie night, and since the Merlyn's had their own private movie theater here, they could watch any movie they so desired. Tonight they were going to be seeing one of Master Malcom's personal favorites 'An Officer and a Slave', then after that they were going to watch 'Masters of the Caribbean'.

They had already had dinner, Master Malcom and Master Tommy eating in the family dinning hall, while Oliver and Roy ate out of dog bowls, lapping at a the Merlyn's leftovers from the previous day, all blended up into a disgusting mush that Oliver would rather starve than eat, not that he had a choice.

During the first film Master Tommy would feed Oliver some of his pop-corn. Oliver felt bad for Roy who was sitting on Master Malcom's lap, and Oliver knew Master Malcom wouldn’t be kind enough to share any real food with the younger man.

The first movie flew by in a hurry, it felt great to be able to escape his current life and watch some other slave be miserable. However 'An Officer and a Slave' was a story with a moral, in which a gay officer falls in love with his own slave and tries to flee to Canada (one of only two countries that didn’t permit slavery of its citizens) only to be caught and become a new slave. It had a some what happy ending though, the former master and his slave got to remain together as slaves to the former master's brother. When Oliver was still a master he use to think it was a fitting, well done ending, but now he didn’t think that so much. Now he thinks it would be better if they had escaped the police and lived out their lives in Canada.

The second film had a lot more action and fantasy in it, as 'Masters of the Caribbean' was a film about Pirates searching for gold as the European settlers set out on a hunt to capture the outlaw bandits and put them in their rightful place in chains. Before becoming a slave he had never really consciously thought about the fact that most big Hollywood films in some way had to do with masters and slaves, even the Disney animated films dealt heavy with such subjects, like in Aladdin how after defeating Jafar Aladdin uses his last wish to enslave Jafar for ever instead of freeing the Genie like he initially promised, which made since, had Aladdin freed the Genie than the movie would be putting dangerous ideals in kids heads.

When the credits finally began to roll it was time for bed, so that Oliver and Master Tommy and Roy could get up tomorrow and play this master and slave game again and again for many days to come.


End file.
